Colin Farrell is descended from the Derek Zoolander tribe of Really, Really, Ridiculously Good-Looking People. In the style department, this is the Irish actor's greatest asset and most glaring weakness: Killer clothes make him ruggedly handsome, while goofy garments turn him into a burnt Thanksgiving dinner—good intentions, terrible ecution. Mix this with the embarrassment hangovers brought on by Daredevil and Alexander, and you get a desperately masculine dude bucking on lame trends. Along the way, a hit indie gave Farrell the self-affirmation he needed, and he eventually stopped trying so damn hard to look like a boss. Here, we trace the Fright Night star's style journey from insecure It Boy to enlightened manly man.

Here, Colin dominates the _laissez-faire _look: a V-neck sans the oord, paired with straight-leg jeans and Cons. Additionally, he still advocates the holy concepts of "showering" and "showing less nipple than one's lady friends."

Photo: Getty Images

The awful 2003 adaptation of _Daredevil _inspires the first of many hair mutations. Despite the chrome-dome and zoot suit combo, Farrell successfully woos the two madres in the background. Yeah, we know, he's in the middle of playing an equally bald villain who kills people with paperclips. Excuses, excuses.

Photo: David Paul Morris/Bloomberg

Phase II:Colin the Almost Great

After dominating the box office with S.W.A.T. and pleasing critics with Intermission, Colin hit GQ's 2003 Men of the Year list. "I'm sweeter, I'm scarier, I'm darker, I'm brighter, I'm cleaner and I'm dirtier than anyone fucking knows," he told us. That's cool, but you left out the part about borrowing suit jackets from Meatloaf.

Photo: Getty Images

Aided by a devil-may-care henley and a Jesus piece, the leading man looks his best at his absolute grimiest. And to assert his undeniable virility, Farrell commands his follicles to produce as much grease as chemically possible. Mission accomplished.

Photo: Getty Images

"Cock-Out Colin" is born. Farrell scores his second GQ cover, divulging that he pulled the 'ole penis-in-the pocket trick while filming _Alexander. _Pushing the hunky grease-ball shtick into troublesome Johnny Depp territory, he adorns himself with man-jewelry and the I-secretly-wish-I-were-a-pirate popover. Even without the nickname, we always pegged him as the penis-trick guy.

Photo: Getty Images

Oof. Still in his slimy Miami Vice period, Colin goes jean-on-jean—a risky mixture that works without the bro jacket, ill-conceived Cuban mobster collar, and denim dress shirt with French cuffs. We didn't even know that last one existed. Impressive, but no.

Photo: David Paul Morris/Bloomberg

Phase III: Trapped in the Phone Booth

Two major disappointments—Alexander and Miami Vice—are added to his résumé. A wounded and, for once, neutered-looking Farrell dons a newsy cap and oversized chambray disguise. Something is very, very wrong if you are Colin Farrell and you look like Carson Daly.

Photo: Getty Images

After taking another hit with Woody Allen's disappointing _Cassandra's Dream, _Colin cleans up. To conquer this skinny tie and slim suit ensemble, he tames the mane and cultivates the goatee. Now he looks more like dirty soulmate Al Pacino. Well done.

Photo: Getty Images

Yeesh—a grown man caves in and belly-flops into the keffiyeh pool. And damn, inappropriate vest timing and shoe-eating jeans, too. He's forgiven, as this photo coincides with 2008's relentlessly awesome In Bruges.

Photo: Getty Images

**Phase IV: Return of the Irishman **

Fueled by the success of In Bruges and a strong supporting role in Crazy Heart, Farrell decides to be good-looking again. Thank the classic bad-boy face fur, rakishly disheveled hair, winning tartan vest, and demise of the keffiyeh.

Photo: Getty Images

The button rule goes something like this: Lose one for work, two for the party, three for the after-party. Colin is at four, count 'em four degrees of unbuttoned-hood. He is not working, partying, or after-partying. So we're pretty sure this is illegal. Also, always properly align the buttons, should you decide to go Fabio.

Photo: Getty Images

Three buttons! The Colin shows restraint without sacrificing his alpha male style. But lose the earrings, faux-badass bandanna cuff, and Lollapalooza wristband, please. Then, and only then, shall we once again call you "Cock-Out Colin."